N-(ω-Amino)alkylaniline derivatives

Abstract

An N-(ω-amino)alkylaniline derivative of the formula: ##STR1## and its pharmaceutically acceptable salts, which are useful as neuroleptic agents and can be prepared by reacting a compound of the formula: ##STR2## with a compound of the formula: H--A [wherein R is hydrogen, C 1 -C 7 alkyl, C 1 -C 7 alkanoyl or aroyl, R 1 is hydrogen, halogen, C 1 -C 7 alkyl or C 1 -C 7 alkoxy, A is ##STR3## (wherein R 2 is hydrogen, halogen, C 1 -C 7 alkyl, C 1 -C 7 alkoxy or trifluoromethyl), ##STR4## (wherein R 2 is as defined above and R 3 is hydrogen, C 1 -C 7 alkyl or C 1 -C 7 alkanoyl), ##STR5## (wherein R 2 is as defined above or ##STR6## (wherein R 2 and R 3 are each as defined above) and n is 2, 3 or 4].

What is claimed is: 
     
       1. An N-(ω-amino)alkylaniline derivative of the formula: ##STR23##wherein R is hydrogen, C 1  -C 7  alkyl, C 1  -C 7  alkanoyl, benzoyl, halobenzoyl or nicotinoyl, R 1  is hydrogen, halogen, C 1  -C 7  alkyl or C 1  -C 7  alkoxy, ##STR24##wherein R 2  is hydrogen, halogen, C 1  -C 7  alkyl, C 1  -C 7  alkoxy or trifluoromethyl and R 3  is hydrogen, C 1  -C 7  alkyl or C 1  -C 7  alkanoyl, ##STR25##wherein R 2  is as defined above or ##STR26##wherein R 2  and R 3  are each as defined above, and n is 2, 3 or 4, and non-toxic pharmaceutically acceptable salts thereof. 
     
     
       2. An (N-(ω-amino)alkylaniline derivative according to claim 1, wherein A is ##STR27## wherein R 2  and R 3  are each as defined in claim 1 and non-toxic pharmaceutically acceptable salts thereof. 
     
     
       3. An N-(ω-amino)alkylaniline derivative according to claim 1, wherein A is ##STR28##wherein R 2  is as defined in claim 1 and non-toxic pharmaceutically acceptable salts thereof. 
     
     
       4. An N-(ω-amino)alkylaniline derivative according to claim 1, wherein A is ##STR29##wherein R 2  and R 3  are each as defined in claim 1 and non-toxic pharmaceutically acceptable salts thereof. 
     
     
       5. An N-(ω-amino)alkylaniline derivative according to claim 1, wherein R is hydrogen, R 1  is fluorine, methyl or methoxy at the para-position, n is 3 and A is ##STR30##wherein R 2  is C 1  -C 3  alkoxy and non-toxic pharmaceutically acceptable salts thereof. 
     
     
       6. An N-(ω-amino)alkylaniline derivative according to claim 1, wherein R is hydrogen or ethyl and R 1  is fluorine, chlorine, methyl or methoxy, 
     
     
       7. An N-(ω-amino)alkylaniline derivative of the formula: ##STR31##wherein R 1  is fluorine, methyl or methoxy, or non-toxic pharmaceutically acceptable salts thereof. 
     
     
       8. A non-toxic pharmaceutical composition comprising an effective neuroleptic amount of at least one of the N-(ω-amino)alkylaniline derivatives of the formula: ##STR32##wherein R is hydrogen, C 1  -C 7  alkyl, C 1  -C 7  alkanoyl, benzoyl, halobenzoyl or nicotinoyl, R 1  is hydrogen, halogen, C 1  -C 7  alkoxy, A is ##STR33##wherein R 2  is hydrogen, halogen, C 1  -C 7  alkyl, C 1  -C 7  alkoxy or trifluoromethyl, ##STR34## wherein R 2  is as defined above and R 3  is hydrogen, C 1  -C 7  alkyl or C 1  -C 7  alkanoyl, ##STR35##wherein R 2  is as defined above or ##STR36##wherein R 2  and R 3  are each as defined above, and n is 2, 3 or 4, and non-toxic pharmaceutically acceptable salts thereof, and a pharmaceutically acceptable carrier. 
     
     
       9. A non-toxic pharmaceutical composition in accordance with claim 8, wherein the N-(ω-amino)alkylaniline derivative has the formula: ##STR37##wherein R 1  is fluorine, chlorine, methyl or methoxy and R 2  is C 1  -C 3  alkoxy, or non-toxic pharmaceutically acceptable acid addition salts thereof. 
     
     
       10. A non-toxic pharmaceutical composition in accordance with claim 8, wherein the N-(ω-amino)alkylaniline derivative has the fomula: ##STR38##wherein R 1  is fluorine, methyl or methoxy, or non-toxic pharmaceutically acceptable salts thereof.